JP2669906B2 - １―アダマンタン誘導体の製造法 - Google Patents

１―アダマンタン誘導体の製造法

Info

Publication number: JP2669906B2
Authority: JP; Japan
Prior art keywords: methyl; solvent; acyloxyadamantane; receptor compound; concentrated sulfuric
Prior art date: 1988-09-07
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Expired - Lifetime

Application number

JP1232678A

Other languages

English (en)

Japanese (ja)

Other versions

JPH02124835A (ja

Inventor

ウィリアムス・ロベール・ピリグリム

ジョエル・ラジール

Original Assignee

サントル・アンテルナショナル・ド・ルシェルシュ・デルマトロジック・セ．イ．エール．デ．

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1988-09-07

Filing date

1989-09-06

Publication date

1997-10-29

1989-09-06 Application filed by サントル・アンテルナショナル・ド・ルシェルシュ・デルマトロジック・セ．イ．エール．デ． filed Critical サントル・アンテルナショナル・ド・ルシェルシュ・デルマトロジック・セ．イ．エール．デ．

1990-05-14 Publication of JPH02124835A publication Critical patent/JPH02124835A/ja

1997-10-29 Application granted granted Critical

1997-10-29 Publication of JP2669906B2 publication Critical patent/JP2669906B2/ja

2012-10-29 Anticipated expiration legal-status Critical

Status Expired - Lifetime legal-status Critical Current

Links

238000004519 manufacturing process Methods 0.000 title claims description 5
ORILYTVJVMAKLC-UHFFFAOYSA-N adamantane Chemical class C1C(C2)CC3CC1CC2C3 ORILYTVJVMAKLC-UHFFFAOYSA-N 0.000 title 1
238000000034 method Methods 0.000 claims abstract description 27
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims abstract description 22
239000002904 solvent Substances 0.000 claims abstract description 18
150000001875 compounds Chemical class 0.000 claims abstract description 14
150000001491 aromatic compounds Chemical class 0.000 claims abstract description 7
125000001931 aliphatic group Chemical group 0.000 claims abstract description 5
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 3
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims description 46
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical group CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 24
ZYLRDAOEBRPIGT-UHFFFAOYSA-N 1-adamantyl acetate Chemical compound C1C(C2)CC3CC2CC1(OC(=O)C)C3 ZYLRDAOEBRPIGT-UHFFFAOYSA-N 0.000 claims description 14
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 9
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 8
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 6
ZEYHEAKUIGZSGI-UHFFFAOYSA-N 4-methoxybenzoic acid Chemical compound COC1=CC=C(C(O)=O)C=C1 ZEYHEAKUIGZSGI-UHFFFAOYSA-N 0.000 claims description 4
YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 4
UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 4
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 4
YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 4
RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 claims description 4
NIFAOMSJMGEFTQ-UHFFFAOYSA-N 4-methoxybenzenethiol Chemical compound COC1=CC=C(S)C=C1 NIFAOMSJMGEFTQ-UHFFFAOYSA-N 0.000 claims description 3
RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 claims description 3
JCXVWUFYQSPUJQ-UHFFFAOYSA-N 1-adamantyl formate Chemical group C1C(C2)CC3CC2CC1(OC=O)C3 JCXVWUFYQSPUJQ-UHFFFAOYSA-N 0.000 claims description 2
AYFJBMBVXWNYLT-UHFFFAOYSA-N 2-bromo-6-methoxynaphthalene Chemical compound C1=C(Br)C=CC2=CC(OC)=CC=C21 AYFJBMBVXWNYLT-UHFFFAOYSA-N 0.000 claims description 2
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 2
QJPJQTDYNZXKQF-UHFFFAOYSA-N 4-bromoanisole Chemical compound COC1=CC=C(Br)C=C1 QJPJQTDYNZXKQF-UHFFFAOYSA-N 0.000 claims description 2
GZFGOTFRPZRKDS-UHFFFAOYSA-N 4-bromophenol Chemical compound OC1=CC=C(Br)C=C1 GZFGOTFRPZRKDS-UHFFFAOYSA-N 0.000 claims description 2
239000002253 acid Substances 0.000 claims description 2
125000002252 acyl group Chemical group 0.000 claims description 2
WJTCGQSWYFHTAC-UHFFFAOYSA-N cyclooctane Chemical compound C1CCCCCCC1 WJTCGQSWYFHTAC-UHFFFAOYSA-N 0.000 claims description 2
239000004914 cyclooctane Substances 0.000 claims description 2
DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 claims description 2
UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 claims description 2
ZWXVPCDIGBXITB-UHFFFAOYSA-N methyl 2-fluoro-4-methoxybenzoate Chemical compound COC(=O)C1=CC=C(OC)C=C1F ZWXVPCDIGBXITB-UHFFFAOYSA-N 0.000 claims description 2
TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 claims description 2
229930192474 thiophene Natural products 0.000 claims description 2
DDIZAANNODHTRB-UHFFFAOYSA-N methyl p-anisate Chemical compound COC(=O)C1=CC=C(OC)C=C1 DDIZAANNODHTRB-UHFFFAOYSA-N 0.000 claims 2
MVLMNZBWGSNOIM-UHFFFAOYSA-N 1-adamantyl propanoate Chemical compound C1C(C2)CC3CC2CC1(OC(=O)CC)C3 MVLMNZBWGSNOIM-UHFFFAOYSA-N 0.000 claims 1
NXWTWYULZRDBSA-UHFFFAOYSA-N 2-fluoro-4-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1F NXWTWYULZRDBSA-UHFFFAOYSA-N 0.000 claims 1
YLDFTMJPQJXGSS-UHFFFAOYSA-N 6-bromo-2-naphthol Chemical compound C1=C(Br)C=CC2=CC(O)=CC=C21 YLDFTMJPQJXGSS-UHFFFAOYSA-N 0.000 claims 1
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 1
YDMAEOFIFQUGFM-UHFFFAOYSA-N methyl 6-(4-hydroxyphenyl)naphthalene-2-carboxylate Chemical compound C1=CC2=CC(C(=O)OC)=CC=C2C=C1C1=CC=C(O)C=C1 YDMAEOFIFQUGFM-UHFFFAOYSA-N 0.000 claims 1
LLKKPBJYOHZIFI-UHFFFAOYSA-N methyl 6-(4-methoxyphenyl)naphthalene-2-carboxylate Chemical compound C1=CC2=CC(C(=O)OC)=CC=C2C=C1C1=CC=C(OC)C=C1 LLKKPBJYOHZIFI-UHFFFAOYSA-N 0.000 claims 1
239000004215 Carbon black (E152) Substances 0.000 abstract 1
229930195733 hydrocarbon Natural products 0.000 abstract 1
150000002430 hydrocarbons Chemical class 0.000 abstract 1
235000011149 sulphuric acid Nutrition 0.000 abstract 1
239000001117 sulphuric acid Substances 0.000 abstract 1
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 28
239000000047 product Substances 0.000 description 24
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
238000002360 preparation method Methods 0.000 description 15
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 14
239000000203 mixture Substances 0.000 description 14
229910052757 nitrogen Inorganic materials 0.000 description 14
238000003756 stirring Methods 0.000 description 14
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 10
230000008018 melting Effects 0.000 description 10
238000002844 melting Methods 0.000 description 10
-1 1-adamantyl group Chemical group 0.000 description 9
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 9
229940075894 denatured ethanol Drugs 0.000 description 9
239000007787 solid Substances 0.000 description 9
239000006227 byproduct Substances 0.000 description 6
238000001035 drying Methods 0.000 description 6
238000001914 filtration Methods 0.000 description 6
239000011521 glass Substances 0.000 description 6
VLLNJDMHDJRNFK-UHFFFAOYSA-N adamantan-1-ol Chemical compound C1C(C2)CC3CC2CC1(O)C3 VLLNJDMHDJRNFK-UHFFFAOYSA-N 0.000 description 5
239000000377 silicon dioxide Substances 0.000 description 5
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
238000006243 chemical reaction Methods 0.000 description 4
238000001704 evaporation Methods 0.000 description 4
230000007935 neutral effect Effects 0.000 description 4
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
239000003480 eluent Substances 0.000 description 3
230000008020 evaporation Effects 0.000 description 3
239000000706 filtrate Substances 0.000 description 3
239000012074 organic phase Substances 0.000 description 3
238000001953 recrystallisation Methods 0.000 description 3
238000010189 synthetic method Methods 0.000 description 3
KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
239000003054 catalyst Substances 0.000 description 2
238000004587 chromatography analysis Methods 0.000 description 2
239000012043 crude product Substances 0.000 description 2
238000004090 dissolution Methods 0.000 description 2
229910052943 magnesium sulfate Inorganic materials 0.000 description 2
235000019341 magnesium sulphate Nutrition 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
239000000725 suspension Substances 0.000 description 2
150000003573 thiols Chemical class 0.000 description 2
QQAMHHZQONQBFZ-UHFFFAOYSA-N 1-(5-bromo-2-methoxyphenyl)adamantane Chemical compound COC1=CC=C(Br)C=C1C1(C2)CC(C3)CC2CC3C1 QQAMHHZQONQBFZ-UHFFFAOYSA-N 0.000 description 1
JIABSGPEWBNGJA-UHFFFAOYSA-N 1-(7-bromo-3-methoxynaphthalen-2-yl)adamantane Chemical compound C1C(C2)CC(C3)CC2CC13C1=CC2=CC(Br)=CC=C2C=C1OC JIABSGPEWBNGJA-UHFFFAOYSA-N 0.000 description 1
KDFLLEJBBCKWJC-UHFFFAOYSA-N 1-[2-[2-(1-adamantyl)-4-methoxyphenyl]sulfanyl-5-methoxyphenyl]adamantane Chemical compound C1C(C2)CC(C3)CC2CC13C1=CC(OC)=CC=C1SC1=CC=C(OC)C=C1C1(C2)CC(C3)CC2CC3C1 KDFLLEJBBCKWJC-UHFFFAOYSA-N 0.000 description 1
HTDQSWDEWGSAMN-UHFFFAOYSA-N 1-bromo-2-methoxybenzene Chemical compound COC1=CC=CC=C1Br HTDQSWDEWGSAMN-UHFFFAOYSA-N 0.000 description 1
VQHPRVYDKRESCL-UHFFFAOYSA-N 1-bromoadamantane Chemical compound C1C(C2)CC3CC2CC1(Br)C3 VQHPRVYDKRESCL-UHFFFAOYSA-N 0.000 description 1
OZNXTQSXSHODFR-UHFFFAOYSA-N 1-chloroadamantane Chemical compound C1C(C2)CC3CC2CC1(Cl)C3 OZNXTQSXSHODFR-UHFFFAOYSA-N 0.000 description 1
CLQFVIUGXYAHAX-UHFFFAOYSA-N 1-propoxyadamantane Chemical compound C1C(C2)CC3CC2CC1(OCCC)C3 CLQFVIUGXYAHAX-UHFFFAOYSA-N 0.000 description 1
NYJXKHIVLGWPCF-UHFFFAOYSA-N 2-(1-adamantyl)-4-bromophenol Chemical compound OC1=CC=C(Br)C=C1C1(C2)CC(C3)CC2CC3C1 NYJXKHIVLGWPCF-UHFFFAOYSA-N 0.000 description 1
JPIGBNKLXFVBTQ-UHFFFAOYSA-N 2-(1-adamantyl)naphthalen-1-ol Chemical compound C1C(C2)CC(C3)CC2CC13C1=C(O)C2=CC=CC=C2C=C1 JPIGBNKLXFVBTQ-UHFFFAOYSA-N 0.000 description 1
APSMUYYLXZULMS-UHFFFAOYSA-N 2-bromonaphthalene Chemical compound C1=CC=CC2=CC(Br)=CC=C21 APSMUYYLXZULMS-UHFFFAOYSA-N 0.000 description 1
RWZRMETXJWTWQW-UHFFFAOYSA-N 3-(1-adamantyl)-4-methoxybenzoic acid Chemical compound COC1=CC=C(C(O)=O)C=C1C1(C2)CC(C3)CC2CC3C1 RWZRMETXJWTWQW-UHFFFAOYSA-N 0.000 description 1
BLOOFHRWAOQRNT-UHFFFAOYSA-N 3-(1-adamantyl)-6-bromonaphthalen-2-ol Chemical compound C1C(C2)CC(C3)CC2CC13C1=CC2=CC(Br)=CC=C2C=C1O BLOOFHRWAOQRNT-UHFFFAOYSA-N 0.000 description 1
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
MSVRGYOYISBGTH-UHFFFAOYSA-N 4-methoxy-2-methylbenzoic acid Chemical compound COC1=CC=C(C(O)=O)C(C)=C1 MSVRGYOYISBGTH-UHFFFAOYSA-N 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
DTVVBPILCSNPCH-UHFFFAOYSA-N COC=1C=C2C=CC(=CC2=CC1)Br.OC=1C=C2C=CC(=CC2=CC1)Br.COC1=CC=C(C=C1)C=1C=C2C=CC(=CC2=CC1)C(=O)OC.OC1=CC=C(C=C1)C=1C=C2C=CC(=CC2=CC1)C(=O)OC Chemical compound COC=1C=C2C=CC(=CC2=CC1)Br.OC=1C=C2C=CC(=CC2=CC1)Br.COC1=CC=C(C=C1)C=1C=C2C=CC(=CC2=CC1)C(=O)OC.OC1=CC=C(C=C1)C=1C=C2C=CC(=CC2=CC1)C(=O)OC DTVVBPILCSNPCH-UHFFFAOYSA-N 0.000 description 1
DADIDNFWHSBAGZ-UHFFFAOYSA-N FC1=C(C(=O)O)C=CC(=C1)O.FC1=C(C(=O)OC)C=CC(=C1)OC.COC1=CC=C(C(=O)OC)C=C1.COC1=CC=C(C(=O)O)C=C1.BrC1=CC=C(C=C1)O.BrC1=CC=C(C=C1)OC Chemical compound FC1=C(C(=O)O)C=CC(=C1)O.FC1=C(C(=O)OC)C=CC(=C1)OC.COC1=CC=C(C(=O)OC)C=C1.COC1=CC=C(C(=O)O)C=C1.BrC1=CC=C(C=C1)O.BrC1=CC=C(C=C1)OC DADIDNFWHSBAGZ-UHFFFAOYSA-N 0.000 description 1
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
150000008065 acid anhydrides Chemical class 0.000 description 1
JTMRNQILBRLKES-UHFFFAOYSA-N adamantan-1-amine adamantane Chemical compound C12(CC3CC(CC(C1)C3)C2)N.C23CC1CC(CC(C2)C1)C3 JTMRNQILBRLKES-UHFFFAOYSA-N 0.000 description 1
230000002411 adverse Effects 0.000 description 1
DKNWSYNQZKUICI-UHFFFAOYSA-N amantadine Chemical compound C1C(C2)CC3CC2CC1(N)C3 DKNWSYNQZKUICI-UHFFFAOYSA-N 0.000 description 1
150000001408 amides Chemical class 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
150000001735 carboxylic acids Chemical class 0.000 description 1
238000004440 column chromatography Methods 0.000 description 1
239000012141 concentrate Substances 0.000 description 1
229940052761 dopaminergic adamantane derivative Drugs 0.000 description 1
238000005886 esterification reaction Methods 0.000 description 1
239000007789 gas Substances 0.000 description 1
238000002955 isolation Methods 0.000 description 1
239000010410 layer Substances 0.000 description 1
LUGWXJMLFWEDAK-UHFFFAOYSA-N methyl 3-(1-adamantyl)-4-methoxybenzoate Chemical compound COC(=O)C1=CC=C(OC)C(C23CC4CC(CC(C4)C2)C3)=C1 LUGWXJMLFWEDAK-UHFFFAOYSA-N 0.000 description 1
NRQNMLFUXLZRQK-UHFFFAOYSA-N methyl 6-[3-(1-adamantyl)-4-hydroxyphenyl]naphthalene-2-carboxylate Chemical compound C1C(C2)CC(C3)CC2CC13C1=CC(C2=CC3=CC=C(C=C3C=C2)C(=O)OC)=CC=C1O NRQNMLFUXLZRQK-UHFFFAOYSA-N 0.000 description 1
PGXNMQBGOVUZNC-UHFFFAOYSA-N methyl 6-[3-(1-adamantyl)-4-methoxyphenyl]naphthalene-2-carboxylate Chemical compound C1C(C2)CC(C3)CC2CC13C1=CC(C2=CC3=CC=C(C=C3C=C2)C(=O)OC)=CC=C1OC PGXNMQBGOVUZNC-UHFFFAOYSA-N 0.000 description 1
150000002825 nitriles Chemical class 0.000 description 1
239000012044 organic layer Substances 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
238000000746 purification Methods 0.000 description 1
239000012429 reaction media Substances 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
239000012265 solid product Substances 0.000 description 1
239000007858 starting material Substances 0.000 description 1
239000000126 substance Substances 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
DTQVDTLACAAQTR-UHFFFAOYSA-N trifluoroacetic acid Substances OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 1
238000001665 trituration Methods 0.000 description 1
238000001291 vacuum drying Methods 0.000 description 1
238000005406 washing Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
- C07C41/18—Preparation of ethers by reactions not forming ether-oxygen bonds
- C07C41/30—Preparation of ethers by reactions not forming ether-oxygen bonds by increasing the number of carbon atoms, e.g. by oligomerisation
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/06—Preparation of carboxylic acid amides from nitriles by transformation of cyano groups into carboxamide groups
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/14—Preparation of carboxylic acid amides by formation of carboxamide groups together with reactions not involving the carboxamide groups
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C319/00—Preparation of thiols, sulfides, hydropolysulfides or polysulfides
- C07C319/14—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of sulfides
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/11—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by reactions increasing the number of carbon atoms
- C07C37/16—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by reactions increasing the number of carbon atoms by condensation involving hydroxy groups of phenols or alcohols or the ether or mineral ester group derived therefrom
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/347—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups
- C07C51/353—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by isomerisation; by change of size of the carbon skeleton
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/30—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
- C07C67/333—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton
- C07C67/343—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/56—Ring systems containing bridged rings
- C07C2603/58—Ring systems containing bridged rings containing three rings
- C07C2603/70—Ring systems containing bridged rings containing three rings containing only six-membered rings
- C07C2603/74—Adamantanes

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Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Chemical Kinetics & Catalysis (AREA)
Engineering & Computer Science (AREA)
Oil, Petroleum & Natural Gas (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

JP1232678A 1988-09-07 1989-09-06 １―アダマンタン誘導体の製造法 Expired - Lifetime JP2669906B2 (ja)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
FR8811706A FR2636061B1 (fr)	1988-09-07	1988-09-07	Procede de preparation de derives de l'adamantane-1
FR8811706		1988-09-07

Publications (2)

Publication Number	Publication Date
JPH02124835A JPH02124835A (ja)	1990-05-14
JP2669906B2 true JP2669906B2 (ja)	1997-10-29

Family

ID=9369798

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP1232678A Expired - Lifetime JP2669906B2 (ja)	1988-09-07	1989-09-06	１―アダマンタン誘導体の製造法

Country Status (16)

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US (1)	US5015758A (de)
EP (1)	EP0358574B1 (de)
JP (1)	JP2669906B2 (de)
AT (1)	ATE85790T1 (de)
AU (1)	AU615331B2 (de)
CA (1)	CA1312075C (de)
DE (1)	DE68904940T2 (de)
DK (1)	DK175205B1 (de)
ES (1)	ES2054063T3 (de)
FI (1)	FI93349C (de)
FR (1)	FR2636061B1 (de)
IE (1)	IE63829B1 (de)
NO (1)	NO170847C (de)
NZ (1)	NZ230575A (de)
PT (1)	PT91640B (de)
ZA (1)	ZA896814B (de)

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US7306674B2 (en) *	2001-01-19	2007-12-11	Chevron U.S.A. Inc.	Nucleation of diamond films using higher diamondoids
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WO2007072217A2 (en) *	2005-06-17	2007-06-28	Medichem, S.A.	Process for the preparation of adapalene and related compounds
RU2309933C1 (ru) *	2006-07-11	2007-11-10	Государственное образовательное учреждение высшего профессионального образования Волгоградский государственный технический университет (ВолгГТУ)	Способ получения адамантилсодержащих производных нафталина
CN100588643C (zh) *	2006-11-02	2010-02-10	南京航空航天大学	一种含有二取代金刚烷基的维甲酸类化合物制备方法
EP2065032A1 (de)	2007-11-27	2009-06-03	Galderma Research & Development	Verfahren zur Herstellung von Adapalen-Gelen
JP5396120B2 (ja) *	2009-03-26	2014-01-22	出光興産株式会社	アダマンタン誘導体
RU2458905C1 (ru) *	2011-06-17	2012-08-20	Федеральное Государственное Бюджетное Учреждение Науки Институт Химии И Химической Технологии Сибирского Отделения Российской Академии Наук (Иххт Со Ран)	Способ получения адамантилсодержащих производных галоидфенолов
CA3002752A1 (en)	2015-10-26	2017-05-04	Oti Lumionics Inc.	Method for patterning a coating on a surface and device including a patterned coating
KR102802931B1 (ko)	2016-12-02	2025-05-08	오티아이 루미오닉스 인크.	방출 영역 위에 배치된 전도성 코팅을 포함하는 디바이스 및 이를 위한 방법
KR102563713B1 (ko)	2017-04-26	2023-08-07	오티아이 루미오닉스 인크.	표면의 코팅을 패턴화하는 방법 및 패턴화된 코팅을 포함하는 장치
CN110832660B (zh)	2017-05-17	2023-07-28	Oti照明公司	在图案化涂层上选择性沉积传导性涂层的方法和包括传导性涂层的装置
US11751415B2 (en)	2018-02-02	2023-09-05	Oti Lumionics Inc.	Materials for forming a nucleation-inhibiting coating and devices incorporating same
US11489136B2 (en)	2018-05-07	2022-11-01	Oti Lumionics Inc.	Method for providing an auxiliary electrode and device including an auxiliary electrode
JP2022508040A (ja)	2018-11-23	2022-01-19	オーティーアイルミオニクスインコーポレーテッド	光透過領域を含むオプトエレクトロニクスデバイス
KR20250160226A (ko)	2019-03-07	2025-11-11	오티아이 루미오닉스 인크.	핵생성 억제 코팅물 형성용 재료 및 이를 포함하는 디바이스
JP7555600B2 (ja)	2019-04-18	2024-09-25	オーティーアイルミオニクスインコーポレーテッド	核生成抑制コーティングを形成するための材料およびそれを組み込んだデバイス
JP7576337B2 (ja)	2019-05-08	2024-11-01	オーティーアイルミオニクスインコーポレーテッド	核生成抑制コーティングを形成するための材料およびそれを組み込んだデバイス
KR20240134240A (ko)	2019-06-26	2024-09-06	오티아이 루미오닉스 인크.	광 회절 특성을 갖는 광 투과 영역을 포함하는 광전자 디바이스
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CN115552643B (zh)	2019-12-24	2025-08-19	Oti照明公司	包含覆盖层的发光装置和其制造方法
US11985841B2 (en)	2020-12-07	2024-05-14	Oti Lumionics Inc.	Patterning a conductive deposited layer using a nucleation inhibiting coating and an underlying metallic coating

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LU85849A1 (fr) *	1985-04-11	1986-11-05	Cird	Derives benzonaphtaleniques,leur procede de preparation et leur application dans les domaines pharmaceutiques et cosmetiques

1988
- 1988-09-07 FR FR8811706A patent/FR2636061B1/fr not_active Expired - Lifetime
1989
- 1989-09-06 IE IE285889A patent/IE63829B1/en not_active IP Right Cessation
- 1989-09-06 FI FI894217A patent/FI93349C/fi active IP Right Grant
- 1989-09-06 ZA ZA896814A patent/ZA896814B/xx unknown
- 1989-09-06 AU AU41065/89A patent/AU615331B2/en not_active Expired
- 1989-09-06 NO NO893585A patent/NO170847C/no not_active IP Right Cessation
- 1989-09-06 PT PT91640A patent/PT91640B/pt not_active IP Right Cessation
- 1989-09-06 CA CA000610413A patent/CA1312075C/fr not_active Expired - Lifetime
- 1989-09-06 DK DK198904413A patent/DK175205B1/da not_active IP Right Cessation
- 1989-09-06 JP JP1232678A patent/JP2669906B2/ja not_active Expired - Lifetime
- 1989-09-06 US US07/403,280 patent/US5015758A/en not_active Expired - Lifetime
- 1989-09-06 NZ NZ230575A patent/NZ230575A/en unknown
- 1989-09-07 ES ES89402446T patent/ES2054063T3/es not_active Expired - Lifetime
- 1989-09-07 EP EP89402446A patent/EP0358574B1/de not_active Expired - Lifetime
- 1989-09-07 AT AT89402446T patent/ATE85790T1/de not_active IP Right Cessation
- 1989-09-07 DE DE8989402446T patent/DE68904940T2/de not_active Expired - Lifetime

Also Published As

Publication number	Publication date
FI93349B (fi)	1994-12-15
ZA896814B (en)	1990-06-27
FR2636061B1 (fr)	1990-11-09
FI894217A0 (fi)	1989-09-06
EP0358574B1 (de)	1993-02-17
PT91640B (pt)	1995-05-31
FR2636061A1 (fr)	1990-03-09
DK441389D0 (da)	1989-09-06
FI93349C (fi)	1995-03-27
NO893585D0 (no)	1989-09-06
DE68904940T2 (de)	1993-08-26
ATE85790T1 (de)	1993-03-15
AU615331B2 (en)	1991-09-26
PT91640A (pt)	1990-03-30
EP0358574A1 (de)	1990-03-14
NO893585L (no)	1990-03-08
CA1312075C (fr)	1992-12-29
ES2054063T3 (es)	1994-08-01
NZ230575A (en)	1991-03-26
DE68904940D1 (de)	1993-03-25
US5015758A (en)	1991-05-14
NO170847C (no)	1992-12-16
NO170847B (no)	1992-09-07
FI894217L (fi)	1990-03-08
IE63829B1 (en)	1995-06-14
JPH02124835A (ja)	1990-05-14
DK175205B1 (da)	2004-07-12
AU4106589A (en)	1990-03-15
IE892858L (en)	1990-03-07
DK441389A (da)	1990-03-08

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Publication	Publication Date	Title
US5015758A (en)	1991-05-14	Process for the preparation of 1-adamantane derivatives
US3746751A (en)	1973-07-17	1-(3-chloro-4-cycloalkylphenyl)-cyclo-alkyl-1-carboxylic acids
WO2023143158A1 (zh)	2023-08-03	苯酚衍生物、及其晶型与制备方法
FR2477536A1 (fr)	1981-09-11	Nouveaux derives acyles de carnitine, procede de preparation de ces derives et leur utilisation therapeutique
KR100224330B1 (ko)	1999-10-15	골관절 질환의 치료에 유용한 n-((4,5-디히드록시-및 4,5,8-트리히드록시-9,10-디히드로-9,10-디옥소-2-안트라센-일)카르보닐)아미노산
EP0303545B1 (de)	1992-06-17	Verfahren zur Herstellung von Phenyläthanolaminotetralinen
US3947519A (en)	1976-03-30	Preparation of optically active allethrorone via allethronyl acid phthalate
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US3931291A (en)	1976-01-06	Preparation of optically active allethrorone via allethronyl acid phthalate
EP0304784B1 (de)	1993-11-10	Verfahren zur Herstellung von Bisphenol-bisacrylaten
US2623065A (en)	1952-12-23	Methods for producing alkoxynaphthoylalkanoic acids
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US3455999A (en)	1969-07-15	Substituted malonic acid monohydrazides
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KR850000569B1 (ko)	1985-04-29	카르니틴의 아실-유도체 제조방법
FR2590894A1 (fr)	1987-06-05	Derives d'acide amino-4 butanoique, leur procede de preparation et leur utilisation
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CH393364A (fr)	1965-06-15	Procédé de préparation de nouveaux dérivés de l'acétanilide
BE864505A (fr)	1978-09-04	Procede de preparation de derives d'acide epoxysuccinique, nouveaux produits ainsi obtenus et leur utilisation notamment pour leur activite anti-inflammatoire
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